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Hydrochloric Acid → N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide

HRID 2283344
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2283344
[CH2:1]([N:4]([CH2:15][CH:16]=[CH2:17])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH2:14])(=[O:7])=[O:6])[CH:2]=[CH2:3].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:24][C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.Cl>O1CCCC1>[CH2:15]([N:4]([CH2:1][CH:2]=[CH2:3])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([Br:24])[CH:26]=1)(=[O:33])=[O:32])(=[O:7])=[O:6])[CH:16]=[CH2:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 17943m-Bromobenzenesulphonyl chlorideHCID 57750998N,N-diallyl-4-aminopyridine-3-sulfonamide

Produkt 1

HCID 57750923N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A mixture of N,N-diallyl-4-aminopyridine-3-sulfonamide (0.25 g, 1.0 mmol) and cesium carbonate (0.82 g, 2.5 mmol) in tetrahydrofuran (10 mL) was stirred for 5 min, 3-bromobenzenesulfonyl chloride (0.17 mL, 1.2 mmol) was added and the reaction was stirred at room temperature over night. Diluted hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (95:5) as the eluent, gave the title compound in 72% yield.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature over night
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ae2624dfd3d4edeb08840337274edaf
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145380B2

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